Identification
- Summary
Desoximetasone is a glucocorticoid used to treat inflammatory and pruritic corticosteroid-responsive dermatoses.
- Brand Names
- Desoxi, Topicort
- Generic Name
- Desoximetasone
- DrugBank Accession Number
- DB00547
- Background
A topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Desoximetasone (DB00547)
- Weight
- Average: 376.4617
Monoisotopic: 376.204987621 - Chemical Formula
- C22H29FO4
- Synonyms
- (11β,16α)-9-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione
- 9alpha-fluoro-16alpha-methyl-delta(1)-corticosterone
- Deoxymethasone
- Desoximetason
- Desoximetasona
- Désoximétasone
- Desoximetasone
- Desoximetasonum
- Desoxymethasone
- External IDs
- A-41-304
- A-41304
- Hoe 304
- HOE-304
- J83.644C
- R 2113
- R-2113
Pharmacology
- Indication
For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Allergic contact dermatitis •••••••••••• •••••••• Treatment of Dermatitis, eczematous •••••••••••• •••••••• Treatment of Plaque psoriasis •••••••••••• ••••• Treatment of Psoriasis •••••••••••• •••••••• Treatment of Corticosteroid-responsive dermatoses •••••••••••• •••••••• - Contraindications & Blackbox Warnings
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Like other topical corticosteroids, desoximetasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Desoximetasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
- Mechanism of action
The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. This is achieved first by the drug binding to the glucocorticoid receptors which then translocates into the nucleus and binds to DNA causing various activations and repressions of genes. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
- Volume of distribution
Not Available
- Protein binding
Bound to plasma proteins in varying degrees.
- Metabolism
Metabolized, primarily in the liver, and then excreted by the kidneys.
- Route of elimination
Corticosteroids are bound to plasma proteins in varying degrees, are metabolized primarily in the liver and excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.Pharmacokinetic studies in men with Desoximetasone Cream USP, 0.25% with tagged desoximetasone showed a total of 5.2% ± 2.9% excretion in urine (4.1% ± 2.3%) and feces (1.1% ± 0.6%)
- Half-life
The half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.
- Clearance
Not Available
- Adverse Effects
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Topically applied desoximetasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The risk or severity of adverse effects can be increased when Desoximetasone is combined with Abatacept. Acarbose The risk or severity of hyperglycemia can be increased when Desoximetasone is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Desoximetasone is combined with Aceclofenac. Acemetacin The risk or severity of gastrointestinal irritation can be increased when Desoximetasone is combined with Acemetacin. Acenocoumarol Desoximetasone may increase the anticoagulant activities of Acenocoumarol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Esperson (sanofi-aventis) / Flubason (sanofi-aventis) / Topicort LP (sanofi-aventis) / Topisolon (sanofi-aventis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desoxi Cream 0.05% Cream 0.05 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 1999-12-22 Not applicable Canada 
Desoxi Cream 0.25% Cream 0.25 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 1999-12-22 Not applicable Canada Desoxi Gel 0.05% Gel 0.05 % Topical Taropharma, A Division Of Taro Pharmaceuticals Inc. 2000-04-13 Not applicable Canada Desoximetasone Ointment 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1985-01-17 Not applicable US 
Topicort Ointment 0.25 % Topical Bausch Health, Canada Inc. 1997-03-24 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desoximetasone Gel 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1998-07-14 Not applicable US Desoximetasone Ointment 2.5 mg/1g Topical Cosette Pharmaceuticals, Inc. 2016-09-01 Not applicable US Desoximetasone Cream 2.5 mg/1g Topical Rebel Distributors 1990-11-30 Not applicable US Desoximetasone Cream 2.5 mg/1g Topical Proficient Rx LP 2006-10-24 Not applicable US Desoximetasone Ointment 2.5 mg/1g Topical Zydus Pharmaceuticals (USA) Inc. 2017-12-05 2022-07-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Desoximetasone 0.05% / Hydroquinone 6% / Tretinoin 0.05% Desoximetasone (0.05 g/100g) + Hydroquinone (6 g/100g) + Tretinoin (0.05 g/100g) Emulsion Topical Sincerus Florida, LLC 2019-05-21 Not applicable US Desoximetasone 0.05% / Niacinamide 4% Desoximetasone (0.05 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-15 Not applicable US Desoximetasone 0.05% / Niacinamide 4% Desoximetasone (0.05 g/100g) + Nicotinamide (4 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-22 Not applicable US Desoximetasone 0.05% / Niacinamide 4% Desoximetasone (0.05 g/100g) + Nicotinamide (4 g/100g) Ointment Topical Sincerus Florida 2019-05-15 Not applicable US
Categories
- ATC Codes
- D07AC03 — Desoximetasone
- D07AC — Corticosteroids, potent (group III)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Dermatologicals
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Pregnadienediols
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Steroids
- Steroids, Fluorinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Hydroxysteroids
- Direct Parent
- 21-hydroxysteroids
- Alternative Parents
- Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-hydroxy ketones / Secondary alcohols / Cyclic alcohols and derivatives / Cyclic ketones show 6 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl fluoride show 21 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:691037)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 4E07GXB7AU
- CAS number
- 382-67-2
- InChI Key
- VWVSBHGCDBMOOT-IIEHVVJPSA-N
- InChI
- InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
- IUPAC Name
- (1S,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-10-hydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- Synthesis Reference
Kieslich, K., Kerb, U. and Raspe, G.; U S . Patent 3,232,839; February 1,1966; assigned to Schering AG, Germany.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014687
- PubChem Compound
- 5311067
- PubChem Substance
- 46506793
- ChemSpider
- 4470604
- BindingDB
- 50103622
- 3255
- ChEBI
- 691037
- ChEMBL
- CHEMBL1766
- ZINC
- ZINC000004212854
- Therapeutic Targets Database
- DAP001185
- PharmGKB
- PA164746011
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Desoximetasone
- FDA label
- Download (93.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Atopic Dermatitis / Psoriasis 1 4 Completed Treatment Psoriasis 2 4 Completed Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 3 Completed Treatment Psoriasis 2 3 Unknown Status Treatment Scalp Psoriasis 1
Pharmacoeconomics
- Manufacturers
- Nycomed us inc
- Perrigo new york inc
- Taro pharmaceuticals inc
- Taro pharmaceuticals north america inc
- Altana inc
- Packagers
- Dispensing Solutions
- E. Fougera and Co.
- Major Pharmaceuticals
- Nycomed Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Qualitest
- Sanofi-Aventis Inc.
- Taro Pharmaceuticals USA
- United Research Laboratories Inc.
- Dosage Forms
Form Route Strength Tablet, coated Oral 500 mg Solution Ophthalmic 3 mg Cream Cream Topical Cream Topical 0.5 mg/1g Cream Topical 2.5 mg/1g Gel Topical 0.5 mg/1g Ointment Topical 0.5 mg/1g Ointment Topical 2.5 mg/1g Spray Topical 2.5 mg/1mL Emulsion Topical Cream Topical Ointment Topical Cream Topical 2.5 MG Ointment Topical 0.25 %w/w Emulsion 0.25 % Ointment Topical Cream Topical 2.5 MG/G Suspension Conjunctival; Ophthalmic Cream Topical 0.05 % Cream Topical 0.25 % Gel Topical 0.05 % Ointment Topical 0.25 % Cream Topical .25 % Cream Topical 2.5 mg / g Gel Topical .05 % Gel Topical .5 mg / g Cream Topical .05 % Cream Topical .5 mg / g Ointment Topical 2.5 mg / g Cream Topical 0.25 %w/w - Prices
Unit description Cost Unit Topicort 0.25% Ointment 60 gm Tube 312.62USD tube Topicort 0.25% Cream 60 gm Tube 230.24USD tube Desoximetasone 0.25% Ointment 60 gm Tube 229.01USD tube Desoximetasone 0.25% Cream 60 gm Tube 204.91USD tube Desoximetasone 0.05% Cream 60 gm Tube 189.99USD tube Desoximetasone 0.05% Gel 60 gm Tube 174.86USD tube Topicort 0.25% Ointment 15 gm Tube 94.14USD tube Topicort 0.05% Gel 15 gm Tube 74.59USD tube Desoximetasone 0.25% Ointment 15 gm Tube 68.86USD tube Topicort 0.25% Cream 15 gm Tube 64.99USD tube Desoximetasone 0.25% Cream 15 gm Tube 59.94USD tube Desoximetasone 0.05% Gel 15 gm Tube 54.46USD tube Desoximetasone 0.05% Cream 15 gm Tube 51.25USD tube Topicort 0.25% cream 4.32USD g Topicort lp 0.05% cream 3.45USD g Desoximetasone 0.05% cream 1.29USD g Topicort 0.25 % Cream 0.73USD g Desoximetasone 0.25% cream 0.63USD g Topicort Mild 0.05 % Cream 0.5USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5990100 No 1999-11-23 2018-03-24 US US8715624 No 2014-05-06 2026-05-26 US US8277780 No 2012-10-02 2028-09-01 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 217 °C PhysProp water solubility 42.1 mg/L Not Available logP 2.35 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.031 mg/mL ALOGPS logP 2.13 ALOGPS logP 2.35 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 13.44 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 101.17 m3·mol-1 Chemaxon Polarizability 40.12 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.9825 Caco-2 permeable + 0.9022 P-glycoprotein substrate Substrate 0.7712 P-glycoprotein inhibitor I Non-inhibitor 0.7281 P-glycoprotein inhibitor II Non-inhibitor 0.7049 Renal organic cation transporter Non-inhibitor 0.7676 CYP450 2C9 substrate Non-substrate 0.8621 CYP450 2D6 substrate Non-substrate 0.9066 CYP450 3A4 substrate Substrate 0.7565 CYP450 1A2 substrate Non-inhibitor 0.927 CYP450 2C9 inhibitor Non-inhibitor 0.9028 CYP450 2D6 inhibitor Non-inhibitor 0.8847 CYP450 2C19 inhibitor Non-inhibitor 0.9486 CYP450 3A4 inhibitor Non-inhibitor 0.6179 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8969 Ames test Non AMES toxic 0.9138 Carcinogenicity Non-carcinogens 0.9264 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.6856 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9473 hERG inhibition (predictor II) Inhibitor 0.5842
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.821793 predictedDarkChem Lite v0.1.0 [M-H]- 192.82176 predictedDeepCCS 1.0 (2019) [M+H]+ 199.081693 predictedDarkChem Lite v0.1.0 [M+H]+ 194.71718 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.481293 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.69824 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Lange K, Kleuser B, Gysler A, Bader M, Maia C, Scheidereit C, Korting HC, Schafer-Korting M: Cutaneous inflammation and proliferation in vitro: differential effects and mode of action of topical glucocorticoids. Skin Pharmacol Appl Skin Physiol. 2000 Mar-Apr;13(2):93-103. [Article]
- Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. [Article]
- Rautanen A, Eriksson JG, Kere J, Andersson S, Osmond C, Tienari P, Sairanen H, Barker DJ, Phillips DI, Forsen T, Kajantie E: Associations of body size at birth with late-life cortisol concentrations and glucose tolerance are modified by haplotypes of the glucocorticoid receptor gene. J Clin Endocrinol Metab. 2006 Nov;91(11):4544-51. Epub 2006 Aug 8. [Article]
- Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [Article]
- Shaw JR, Gabor K, Hand E, Lankowski A, Durant L, Thibodeau R, Stanton CR, Barnaby R, Coutermarsh B, Karlson KH, Sato JD, Hamilton JW, Stanton BA: Role of glucocorticoid receptor in acclimation of killifish (Fundulus heteroclitus) to seawater and effects of arsenic. Am J Physiol Regul Integr Comp Physiol. 2007 Feb;292(2):R1052-60. Epub 2006 Oct 12. [Article]
- Sher L: Combined dexamethasone suppression-corticotropin-releasing hormone stimulation test in studies of depression, alcoholism, and suicidal behavior. ScientificWorldJournal. 2006 Oct 31;6:1398-404. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55